My nipples hurt terribly when he latches and now even when something rubs.

I can no longer manually extract milk nor with pump only some clear liquid on one side. I think my milk is gone.

He wants to nurse more, but also eat and drink more normal foods.

He already did great with nights he goes to sleep with dh without nursing and sleeps through- But day times and when he wakes up he wants to nurse. I could probably skip waking up and daytime without issue, but naptime is something else. He wont sleep.

He does not nurse at set times aside from wake up and nap time. It hurts when he latches not anymore or less based on duration of nursing.

Everything I read talks about cutting our feedings but he is not regular some days when busy he does not nurse at all other days he comes up all days long.

Shoudl I just stop him cold turkes at this point? Any suggestions for nap time?

I had pretty much the same problem with our back then almost 11 months old daughter. We're expecting our second baby in September so my milk hadn't dried up completely then but I knew it was going away super fast.
Other than you I had to nurse her at bedtime, otherwise she wouldn't go to sleep. Same for naps...and she wanted milk (she basically greeted my husband making the milk sign in her crib in the mornings) as soon as she woke up.
I started the whole weaning business by giving her cows milk (I know, a little early at 11 months but she refused formula) during the day and only nursed her at bedtime/naptime. She didn't really get much milk at this point anyway, it was more like comfort suckling - comfort for her, painful for me. It took her about a week to accept the whole milk but from then on she loved it!
Surprisingly, weaning her was not as hard as I thought. For nighttime I just gave her a sippy cup with whole milk and once she was done with that I gave her a bath like every night and afterwards held her in my arms while I sang to her. Singing in an almost dark room is now our new bedtime ritual after playground and bath time instead of nursing.
Naps have been a different story, for a long time (about 6 weeks) she only wanted to go to sleep in her stroller, so I had to "walk her to sleep". And even though that wasn't the perfect solution I would have been willing to go with it. But she didn't stay asleep long enough after about 4 weeks - I guess our stroller - as great as it is - is still not as comfy as her bed. So here's what I did: I skipped her morning nap and waited until she was super tired. Then I gave her a little bit of milk in her sippy cup, held her in my arms for a minute or so and then put her to bed. She didn't sleep, just held her little glowing seahorse and looked at me happily. After a while I left and she started crying. Man that was hard, but she stopped after less than 5 minutes and I do think that doesn't count as crying it out. I mean, if I never let my kid cry I'll never get anything done! I've done this 3 times now and it has worked every time so far. She now naps once only for about 2-3 hours versus 2 naps for 1-2 hours each but I'm okay with that.
As for mornings, I now give her a sippy cup with whole milk first thing when she wakes up and she's fine with that...happy actually. She makes little happy singing noises as soon as she sees the sippy cup coming. I think since she hardly got any milk from my breasts anymore anyway, she was more ready to accept the alternative.
I hope that helps. Good luck!

Yeah, our daughter will also wake up if you take her out of the stroller or car seat.
Who would have thought that nap time would be so hard?! Like I said, just wait until he's really tired, snuggle a little and then put him in bed. He might surprise you and go to sleep. Trust me, I never thought it would work like it did with our daughter!